DL-4-Aminophenylglycine is a non-proteinogenic amino acid derivative featuring a glycine backbone substituted with a para-aminophenyl side chain, providing an aniline-type aromatic functionality alongside the amino acid core. The molecule contains both an amino group and a carboxyl group (as the free amino acid form implied by the name), with stereochemistry expressed as DL to indicate a racemic mixture at the amino acid stereocenter when applicable. DL-4-Aminophenylglycine is used as a building block in peptide and peptidomimetic synthesis and in chemical biology workflows where an aromatic, aniline-like side chain can serve as a handle for conjugation, coupling, or structure-activity studies.
CAT No: CP09901
DL-4-Aminophenylglycine is a DL (racemic) amino acid derivative featuring a phenylglycine backbone bearing a para-amino substituent on the aromatic ring, providing both an α-amino acid functionality and an additional aniline-type primary amine. The molecule contains a carboxylic acid and a stereogenic center at the glycine carbon, yielding two enantiomers that can be handled as a racemate for intermediate preparation or separated when enantioselective outcomes are required. The aromatic amine can participate in electrophilic aromatic transformations, diazotization chemistry, and nucleophilic acylation, while the amino acid group supports standard peptide coupling and orthogonal protection strategies. The combination of side-chain aniline reactivity and amino acid coupling compatibility makes DL-4-aminophenylglycine a practical chiral-building-block precursor and a functionalized residue for peptide and peptidomimetic construction.
1. Peptide Synthesis
DL-4-Aminophenylglycine is used in peptide synthesis workflows where an amino acid residue with a pendant aniline enables incorporation of aryl-functionalized motifs into linear peptides and protected peptide fragments. The α-carboxylic acid and α-amino group support conventional peptide coupling after appropriate N-protection (for example, carbamate or sulfonamide protection) to control chemoselectivity relative to the aromatic primary amine. The para-amino substituent can be protected orthogonally or left protected during coupling and then deprotected to expose a reactive aniline for subsequent derivatization. Downstream peptide analogs prepared from this residue can be used to probe aromatic side-chain effects on folding, binding, and stability in biochemical research and molecular design programs.
2. Side-Chain Functionalization
DL-4-Aminophenylglycine is applied in synthetic organic chemistry and chemical biology to generate aniline-bearing intermediates for further functional group transformation on the aromatic ring. The para-primary amine can be converted into amides, ureas, sulfonamides, azo-linked motifs via diazotization chemistry, or aromatic heterocycles through nucleophilic substitution and cyclization sequences. The amino acid framework provides a handle for controlled protection and deprotection, enabling sequential modification where the aromatic amine is derivatized while the carboxylate and α-amino functionality are maintained for later coupling steps. Functionalized derivatives derived from this residue can serve as late-stage modification targets in SAR studies, fragment elaboration, and scaffold diversification.
3. Chiral Building Block Development
DL-4-Aminophenylglycine is suitable for chiral building block development because it contains a stereogenic center that can be resolved into enantiopure material or carried through as a racemate when stereochemical purity is not the primary requirement. The presence of the aromatic para-amine allows installation of stereochemical control elements through selective protection and formation of derivatives used in resolution or stereoselective downstream transformations. The amino acid functionality supports conversion into protected amino acid derivatives (N-protected, optionally esterified at the carboxyl group) that are compatible with peptide coupling chemistry and chiral intermediate workflows. Enantiomerically enriched or derivatized forms can then be used to construct stereochemically defined peptidomimetics and chiral SAR libraries.
4. Bioconjugation Chemistry
DL-4-Aminophenylglycine is used in bioconjugation and chemical biology contexts where an aniline-type primary amine can be transformed into conjugation-ready electrophiles or handles for linker attachment. The aromatic amine can be functionalized into amide-forming derivatives, activated carbonate/ester intermediates, or dye/biomolecule-reactive moieties after appropriate protection of the amino acid termini. The amino acid backbone can be incorporated into peptide linkers or used as a residue in affinity tags, enabling attachment to proteins, peptides, or other biomolecular scaffolds through amide bond formation and controlled deprotection. Resulting conjugates and labeled biomolecules can support analytical research, binding studies, and mechanistic investigations that require defined aromatic amine chemistry.
5. Pharmaceutical Intermediate Preparation
DL-4-Aminophenylglycine is relevant to pharmaceutical intermediate preparation and specialty chemical production where functionalized amino acid derivatives serve as feedstocks for medicinal chemistry and process chemistry routes. The dual presence of an amino acid carboxyl group and a para-amino aromatic side chain supports conversion into protected amino acid intermediates, including esterified and N-protected forms that are compatible with coupling and downstream transformations. The aromatic amine can be used to access key heteroatom-rich motifs encountered in small-molecule synthesis, including substituted anilines and amide-rich pharmacophore fragments. Process-oriented utilization can include scalable protection/deprotection strategies and intermediate staging that aligns with peptide-like coupling steps and fine chemical synthesis requirements.
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